CN1058263C - 羟甲基乙内酰脲的制备方法 - Google Patents

羟甲基乙内酰脲的制备方法 Download PDF

Info

Publication number: CN1058263C
Authority: CN; China
Prior art keywords: reactant; glycolylurea; described method; formaldehyde source; hydantoin
Prior art date: 1992-05-21
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired - Fee Related

Application number

CN93105790A

Other languages

English (en)

Chinese (zh)

Other versions

CN1080635A (zh

Inventor

T·E·法瑞纳

D·A·伯格

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Lonza AG

Lonza LLC

Original Assignee

Lonza LLC

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1992-05-21

Filing date

1993-05-21

Publication date

2000-11-08

1993-05-21 Application filed by Lonza LLC filed Critical Lonza LLC

1994-01-12 Publication of CN1080635A publication Critical patent/CN1080635A/zh

2000-11-08 Application granted granted Critical

2000-11-08 Publication of CN1058263C publication Critical patent/CN1058263C/zh

2013-05-21 Anticipated expiration legal-status Critical

Status Expired - Fee Related legal-status Critical Current

Links

238000004519 manufacturing process Methods 0.000 title description 2
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims abstract description 233
239000000376 reactant Substances 0.000 claims abstract description 87
238000000034 method Methods 0.000 claims abstract description 64
DZNJSBHVDXLTIK-UHFFFAOYSA-N 1-(hydroxymethyl)imidazolidine-2,4-dione Chemical compound OCN1CC(=O)NC1=O DZNJSBHVDXLTIK-UHFFFAOYSA-N 0.000 claims abstract description 44
WJRBRSLFGCUECM-UHFFFAOYSA-N hydantoin Chemical compound O=C1CNC(=O)N1 WJRBRSLFGCUECM-UHFFFAOYSA-N 0.000 claims abstract description 44
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 25
239000007787 solid Substances 0.000 claims abstract description 19
238000010924 continuous production Methods 0.000 claims abstract description 5
239000000203 mixture Substances 0.000 claims description 38
238000003756 stirring Methods 0.000 claims description 23
SIQZJFKTROUNPI-UHFFFAOYSA-N 1-(hydroxymethyl)-5,5-dimethylhydantoin Chemical compound CC1(C)N(CO)C(=O)NC1=O SIQZJFKTROUNPI-UHFFFAOYSA-N 0.000 claims description 18
238000006243 chemical reaction Methods 0.000 claims description 18
230000004927 fusion Effects 0.000 claims description 16
229930040373 Paraformaldehyde Natural products 0.000 claims description 15
229920002866 paraformaldehyde Polymers 0.000 claims description 15
238000010438 heat treatment Methods 0.000 claims description 11
230000018044 dehydration Effects 0.000 claims description 10
238000006297 dehydration reaction Methods 0.000 claims description 10
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 9
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims description 8
239000000155 melt Substances 0.000 claims description 5
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 4
235000017557 sodium bicarbonate Nutrition 0.000 claims description 4
229910000030 sodium bicarbonate Inorganic materials 0.000 claims description 4
229910052728 basic metal Inorganic materials 0.000 claims description 3
150000003818 basic metals Chemical group 0.000 claims description 3
150000003839 salts Chemical class 0.000 claims description 3
235000017550 sodium carbonate Nutrition 0.000 claims description 2
229910000029 sodium carbonate Inorganic materials 0.000 claims description 2
235000011121 sodium hydroxide Nutrition 0.000 claims description 2
230000006837 decompression Effects 0.000 claims 4
238000010923 batch production Methods 0.000 abstract 1
229940091173 hydantoin Drugs 0.000 abstract 1
239000000047 product Substances 0.000 description 21
238000002360 preparation method Methods 0.000 description 8
208000005156 Dehydration Diseases 0.000 description 7
239000007864 aqueous solution Substances 0.000 description 6
-1 1-or 3-methylol-5 Chemical compound 0.000 description 5
239000011521 glass Substances 0.000 description 5
239000007791 liquid phase Substances 0.000 description 4
239000000463 material Substances 0.000 description 4
WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 4
238000002156 mixing Methods 0.000 description 4
238000012545 processing Methods 0.000 description 4
239000000243 solution Substances 0.000 description 4
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
238000013461 design Methods 0.000 description 3
239000007788 liquid Substances 0.000 description 3
239000012429 reaction media Substances 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
238000007711 solidification Methods 0.000 description 3
230000008023 solidification Effects 0.000 description 3
239000002904 solvent Substances 0.000 description 3
239000000725 suspension Substances 0.000 description 3
OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 2
USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 2
239000005695 Ammonium acetate Substances 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
239000003513 alkali Substances 0.000 description 2
229940043376 ammonium acetate Drugs 0.000 description 2
235000019257 ammonium acetate Nutrition 0.000 description 2
238000004458 analytical method Methods 0.000 description 2
239000007795 chemical reaction product Substances 0.000 description 2
239000003153 chemical reaction reagent Substances 0.000 description 2
239000011248 coating agent Substances 0.000 description 2
238000000576 coating method Methods 0.000 description 2
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
229910000041 hydrogen chloride Inorganic materials 0.000 description 2
230000003647 oxidation Effects 0.000 description 2
238000007254 oxidation reaction Methods 0.000 description 2
TZMFJUDUGYTVRY-UHFFFAOYSA-N pentane-2,3-dione Chemical compound CCC(=O)C(C)=O TZMFJUDUGYTVRY-UHFFFAOYSA-N 0.000 description 2
238000003918 potentiometric titration Methods 0.000 description 2
239000002994 raw material Substances 0.000 description 2
239000000126 substance Substances 0.000 description 2
ODIGIKRIUKFKHP-UHFFFAOYSA-N (n-propan-2-yloxycarbonylanilino) acetate Chemical compound CC(C)OC(=O)N(OC(C)=O)C1=CC=CC=C1 ODIGIKRIUKFKHP-UHFFFAOYSA-N 0.000 description 1
REAABIMOJIFWGK-UHFFFAOYSA-N CCN(C(O)O)C(N(C)C(CO)=O)=O Chemical compound CCN(C(O)O)C(N(C)C(CO)=O)=O REAABIMOJIFWGK-UHFFFAOYSA-N 0.000 description 1
ULDBLWYSEKEWAS-UHFFFAOYSA-N CCN(CO)C(N(C)C(CO)=O)=O Chemical compound CCN(CO)C(N(C)C(CO)=O)=O ULDBLWYSEKEWAS-UHFFFAOYSA-N 0.000 description 1
ZERPWFUCOZGAPQ-UHFFFAOYSA-N CCNC(N(C)C(CO)=O)=O Chemical compound CCNC(N(C)C(CO)=O)=O ZERPWFUCOZGAPQ-UHFFFAOYSA-N 0.000 description 1
AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical class ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 1
MAYBWQDXJVWQLO-UHFFFAOYSA-N N-carbamoyl-2-hydroxy-N-(hydroxymethyl)acetamide Chemical compound OCN(C(=O)N)C(CO)=O MAYBWQDXJVWQLO-UHFFFAOYSA-N 0.000 description 1
IZVGPDXGCRNKKL-UHFFFAOYSA-N N1CCCCC1.CC1=CC(=NN1)C Chemical class N1CCCCC1.CC1=CC(=NN1)C IZVGPDXGCRNKKL-UHFFFAOYSA-N 0.000 description 1
UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
206010044565 Tremor Diseases 0.000 description 1
238000010521 absorption reaction Methods 0.000 description 1
239000002253 acid Substances 0.000 description 1
238000007792 addition Methods 0.000 description 1
239000002386 air freshener Substances 0.000 description 1
239000004411 aluminium Substances 0.000 description 1
229910052782 aluminium Inorganic materials 0.000 description 1
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
239000005030 aluminium foil Substances 0.000 description 1
238000003556 assay Methods 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
238000001816 cooling Methods 0.000 description 1
HPYNZHMRTTWQTB-UHFFFAOYSA-N dimethylpyridine Natural products CC1=CC=CN=C1C HPYNZHMRTTWQTB-UHFFFAOYSA-N 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
239000004744 fabric Substances 0.000 description 1
239000003925 fat Substances 0.000 description 1
JEIPFZHSYJVQDO-UHFFFAOYSA-N ferric oxide Chemical compound O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
238000011049 filling Methods 0.000 description 1
238000004817 gas chromatography Methods 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
238000009413 insulation Methods 0.000 description 1
239000004816 latex Substances 0.000 description 1
229920000126 latex Polymers 0.000 description 1
239000006210 lotion Substances 0.000 description 1
238000005259 measurement Methods 0.000 description 1
OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Natural products OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 1
244000005700 microbiome Species 0.000 description 1
239000011707 mineral Substances 0.000 description 1
235000010755 mineral Nutrition 0.000 description 1
238000011017 operating method Methods 0.000 description 1
239000003973 paint Substances 0.000 description 1
229920000642 polymer Polymers 0.000 description 1
WFIZEGIEIOHZCP-UHFFFAOYSA-M potassium formate Chemical compound [K+].[O-]C=O WFIZEGIEIOHZCP-UHFFFAOYSA-M 0.000 description 1
229910001950 potassium oxide Inorganic materials 0.000 description 1
239000002243 precursor Substances 0.000 description 1
230000001681 protective effect Effects 0.000 description 1
239000002516 radical scavenger Substances 0.000 description 1
230000001105 regulatory effect Effects 0.000 description 1
230000000630 rising effect Effects 0.000 description 1
230000035945 sensitivity Effects 0.000 description 1
239000002453 shampoo Substances 0.000 description 1
239000000344 soap Substances 0.000 description 1
239000012265 solid product Substances 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1
230000009967 tasteless effect Effects 0.000 description 1
238000010998 test method Methods 0.000 description 1
239000004753 textile Substances 0.000 description 1
238000005406 washing Methods 0.000 description 1
239000002023 wood Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D233/72—Two oxygen atoms, e.g. hydantoin
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D233/72—Two oxygen atoms, e.g. hydantoin
- C07D233/76—Two oxygen atoms, e.g. hydantoin with substituted hydrocarbon radicals attached to the third ring carbon atom
- C07D233/78—Radicals substituted by oxygen atoms

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Paper (AREA)
Plural Heterocyclic Compounds (AREA)
Diaphragms For Electromechanical Transducers (AREA)
Manufacturing Of Micro-Capsules (AREA)
Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Phenolic Resins Or Amino Resins (AREA)

CN93105790A 1992-05-21 1993-05-21 羟甲基乙内酰脲的制备方法 Expired - Fee Related CN1058263C (zh)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US07/887,356 US5252744A (en)	1992-05-21	1992-05-21	Process for preparing methylolhydantoins
US07/887,356		1992-05-21

Publications (2)

Publication Number	Publication Date
CN1080635A CN1080635A (zh)	1994-01-12
CN1058263C true CN1058263C (zh)	2000-11-08

Family

ID=25390977

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CN93105790A Expired - Fee Related CN1058263C (zh)	1992-05-21	1993-05-21	羟甲基乙内酰脲的制备方法

Country Status (19)

Country	Link
US (1)	US5252744A (da)
EP (1)	EP0571904B1 (da)
JP (1)	JP2604537B2 (da)
KR (1)	KR100286244B1 (da)
CN (1)	CN1058263C (da)
AT (1)	ATE129494T1 (da)
AU (1)	AU668719B2 (da)
BR (1)	BR9301947A (da)
CA (1)	CA2096675C (da)
DE (1)	DE69300697T2 (da)
DK (1)	DK0571904T3 (da)
ES (1)	ES2081162T3 (da)
GR (1)	GR3018310T3 (da)
HU (1)	HU213034B (da)
PL (1)	PL299027A1 (da)
RU (1)	RU2105760C1 (da)
TW (1)	TW370526B (da)
UA (1)	UA27790C2 (da)
ZA (1)	ZA933465B (da)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5616722A (en) *	1995-12-05	1997-04-01	Mcintyre Group, Ltd.	Antimicrobial solution of formaldehyde substituted hydantoin and process for preparation
KR20050058426A (ko) *	2002-08-20	2005-06-16	론자 인코포레이티드	알데히드 공여자와 탈히드로아세트산의 안정한, 저 유리 포름알데히드의, 상승적인 항균성 조성물
CN102718717B (zh) *	2012-06-15	2015-03-11	河北鑫淘源环保科技有限公司	一种固体1,3-二羟甲基-5,5-二甲基海因的烘干方法
ES2848536T3 (es)	2012-08-21	2021-08-10	Lonza Llc	Método para eliminar compuestos de sulfhidrilo
CN114014811A (zh) *	2021-12-13	2022-02-08	陕西省石油化工研究设计院	一种1,3-二羟甲基-5,5-二甲基乙内酰脲的制备方法

Citations (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3987184A (en) *	1974-06-07	1976-10-19	Glyco Chemicals, Inc.	Dimethylol dimethylhydantoin solution
EP0391645A1 (en) *	1989-04-05	1990-10-10	Lonza Inc.	Process for preparing methylolated hydantoins
WO1991013617A1 (en) *	1990-03-05	1991-09-19	The Mcintyre Group, Ltd.	Antimicrobial preservative system comprising a formaldehyde substituted hydantoin

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5036095A (en) *	1989-11-14	1991-07-30	Guy Andermann	Therapeutic use of DMDM Hydantoin

1992
- 1992-05-21 US US07/887,356 patent/US5252744A/en not_active Expired - Lifetime
1993
- 1993-05-18 ZA ZA933465A patent/ZA933465B/xx unknown
- 1993-05-20 RU RU93005165/04A patent/RU2105760C1/ru not_active IP Right Cessation
- 1993-05-20 AU AU38720/93A patent/AU668719B2/en not_active Ceased
- 1993-05-20 BR BR9301947A patent/BR9301947A/pt not_active IP Right Cessation
- 1993-05-20 KR KR1019930008898A patent/KR100286244B1/ko not_active Expired - Fee Related
- 1993-05-20 HU HU9301479A patent/HU213034B/hu not_active IP Right Cessation
- 1993-05-20 CA CA002096675A patent/CA2096675C/en not_active Expired - Fee Related
- 1993-05-21 EP EP93108286A patent/EP0571904B1/en not_active Expired - Lifetime
- 1993-05-21 DK DK93108286.1T patent/DK0571904T3/da active
- 1993-05-21 PL PL29902793A patent/PL299027A1/xx unknown
- 1993-05-21 ES ES93108286T patent/ES2081162T3/es not_active Expired - Lifetime
- 1993-05-21 DE DE69300697T patent/DE69300697T2/de not_active Expired - Fee Related
- 1993-05-21 CN CN93105790A patent/CN1058263C/zh not_active Expired - Fee Related
- 1993-05-21 JP JP5156030A patent/JP2604537B2/ja not_active Expired - Fee Related
- 1993-05-21 AT AT93108286T patent/ATE129494T1/de not_active IP Right Cessation
- 1993-05-28 UA UA93005389A patent/UA27790C2/uk unknown
- 1993-07-22 TW TW082105858A patent/TW370526B/zh active
1995
- 1995-12-05 GR GR950403429T patent/GR3018310T3/el unknown

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3987184A (en) *	1974-06-07	1976-10-19	Glyco Chemicals, Inc.	Dimethylol dimethylhydantoin solution
EP0391645A1 (en) *	1989-04-05	1990-10-10	Lonza Inc.	Process for preparing methylolated hydantoins
WO1991013617A1 (en) *	1990-03-05	1991-09-19	The Mcintyre Group, Ltd.	Antimicrobial preservative system comprising a formaldehyde substituted hydantoin

Also Published As

Publication number	Publication date
ZA933465B (en)	1994-02-08
EP0571904B1 (en)	1995-10-25
EP0571904A1 (en)	1993-12-01
UA27790C2 (uk)	2000-10-16
RU2105760C1 (ru)	1998-02-27
ATE129494T1 (de)	1995-11-15
DE69300697T2 (de)	1996-05-30
JPH072791A (ja)	1995-01-06
JP2604537B2 (ja)	1997-04-30
CA2096675A1 (en)	1993-11-22
CN1080635A (zh)	1994-01-12
AU668719B2 (en)	1996-05-16
AU3872093A (en)	1993-11-25
BR9301947A (pt)	1993-11-30
GR3018310T3 (en)	1996-03-31
KR930023351A (ko)	1993-12-18
HUT64312A (en)	1993-12-28
TW370526B (en)	1999-09-21
HU213034B (en)	1997-01-28
DE69300697D1 (de)	1995-11-30
CA2096675C (en)	1997-02-18
KR100286244B1 (ko)	2001-04-16
DK0571904T3 (da)	1996-02-05
PL299027A1 (en)	1994-01-10
ES2081162T3 (es)	1996-02-16
US5252744A (en)	1993-10-12

Legal Events

Date	Code	Title
1994-01-12	C06	Publication
1994-01-12	PB01	Publication
1995-08-30	C10	Entry into substantive examination
1995-08-30	SE01	Entry into force of request for substantive examination
2000-11-08	C14	Grant of patent or utility model
2000-11-08	GR01	Patent grant
2005-07-20	C19	Lapse of patent right due to non-payment of the annual fee
2005-07-20	CF01	Termination of patent right due to non-payment of annual fee

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